Characterization of rare trifucosylated human milk oligosaccharides by cryogenic infrared ion spectroscopy (CIRIS)

Anal Bioanal Chem. 2025 Nov;417(27):6231-6239. doi: 10.1007/s00216-025-06114-5. Epub 2025 Sep 26.

Abstract

While approximately 200 human milk oligosaccharide structures (HMOs) have been completely characterized, the precise isomeric structures of even more HMOs remain ambiguous. To address this analytical challenge, we employ tandem mass spectrometry (i.e., MS/MS) coupled with cryogenic infrared ion spectroscopy (CIRIS) to characterize and identify novel fucosylated HMOs isolated from pooled human milk. In this approach, the precise structure of isomeric precursor molecules purified by liquid chromatography (LC) is identified by IR fingerprinting their fragments. Using this technique, we have identified four novel isomers of trifucosylated oligosaccharides (i.e., trifucosyl-lacto-N-heptaoses and trifucosyl-lacto-N-neoheptaoses), some of which could not have been produced by previously known biosynthetic pathways for HMO synthesis in the mammary gland.

Keywords: Cryogenic IR spectroscopy; Glycan analysis; Human milk oligosaccharides; Mass spectrometry; Structural analysis of glycomics; TF-LNT.

MeSH terms

  • Chromatography, Liquid / methods
  • Female
  • Fucose / chemistry
  • Humans
  • Milk, Human* / chemistry
  • Oligosaccharides / analysis
  • Oligosaccharides / chemistry
  • Spectrophotometry, Infrared / methods

Substances

  • Oligosaccharides
  • Fucose